Flavone compounds

Abstract

A compound of general formula (I): ##STR1## in which: R.sub.1 represents alkyl,X represents oxygen, --CHR'-- or --CR'.dbd.,R' is chosen from hydrogen and alkyl,R.sub.2 represents optionally substituted alkyl as is defined in the description, cycloalkyl or polycycloalkyl as are defined in the description,R.sub.3 represents hydrogen or hydroxyl,Alk represents alkylene, andY is as defined in the description,and medicinal products containing the same are useful as PDE IV inhibitors.

Claims

1. A compound selected from those of general formula (I): ##STR25## in which R.sub.1 represents alkyl,

R.sub.2 is chosen from the group consisting of

cyclic hydrocarbon containing 3 to 9 carbon atoms inclusive, optionally containing one or more intracyclic double bonds and optionally substituted with one or more halogen, alkyl, alkoxy and/or hydroxyl,

polycyclic hydrocarbon containing 6 to 15 carbon atoms inclusive, optionally containing one or more double bonds and optionally substituted with one or more halogen, alkyl, alkoxy, and/or hydroxyl,

linear or branched hydrocarbon containing 1 to 13 carbon atoms inclusive, optionally containing one or more unsaturations in the form of double and/or triple bonds and optionally substituted with one or more halogen, hydroxyl, alkoxy, aryl, heteroaryl radicals, cyclic hydrocarbon radicals defined as above and/or polycyclic hydrocarbon radicals defined above,

R.sub.3 is chosen from hydrogen and hydroxyl,

Alk represents linear or branched alkylene containing 1 to 6 carbon atoms, inclusive

X is chosen from oxygen, --CR,'.dbd. and --CHR'--,

R' is chosen from hydrogen and alkyl, and

Y is chosen from the group consisting of: ##STR26## in which: Z.sub.1 represents oxygen or sulfur,

Z.sub.2 represents oxygen, sulfur,.dbd.N--OR.sub.4, or ##STR27## R.sub.4, R.sub.4 ' and R.sub.4 ", which may be identical or different, are chosen, independently of one another, from hydrogen, alkyl optionally substituted with aryl or heteroaryl, aryl, heteroaryl, and cycloalkyl,

R.sub.5, R.sub.5 ' and R.sub.5 ", which may be identical or different, are chosen, independently of one another, from alkyl optionally substituted with aryl or heteroaryl, aryl, heteroaryl, and cycloalkyl,

A represents a saturated or unsaturated mono- or bicyclic radical containing a total of 5 to 10 atoms (among which, in total, 1, 2, or 3 of them can optionally represent a hetero atom chosen from oxygen, sulfur, and/or nitrogen) and optionally substituted with one or more halogen, alkyl, and/or alkoxy, and

Hal represents halogen,

the term "alkyl" represents alkyl containing 1 to 6 carbon atoms inclusive in an unbranched or branched chain, and optionally substituted with one or more halogen, hydroxyl, and/or alkoxy,

the term "alkoxy" represents alkoxy containing 1 to 6 carbon atoms inclusive in an unbranched or branched chain, and optionally substituted with one or more halogen and/or hydroxyl,

the term "aryl" represents phenyl or naphthyl, optionally substituted with one or more halogen, alkyl, hydroxyl, and/or alkoxy,

the term "heteroaryl" represents a radical chosen from furyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, indolyl, quinolyl, isoquinolyl and quinazolinyl, optionally substituted with one or more halogen, alkyl, hydroxyl, and/or alkoxy,

the term "halogen atom" represents fluorine, chlorine, bromine, or iodine,

the term "cycloalkyl" represents a cyclic and saturated hydrocarbon containing 3 to 8 carbon atoms inclusive and optionally substituted with one or more halogen, and/or alkyl, hydroxyl, and/or alkoxy,

its possible optical and/or geometric isomers in pure form or as a mixture, and its possible addition salts with a pharmaceutically-acceptable acid or base, with the proviso, however, that when R.sub.1 represents methyl, X represents oxygen, R.sub.3 represents hydrogen, Alk represents methylene, and Y represents C(Z.sub.1)OR.sub.4, wherein Z.sub.1 represents oxygen and R.sub.4 represents ethyl, then R.sub.2 is other than unsubstituted alkyl.

2. A compound as claimed in claim 1 in which X represents oxygen, its possible optical and/or geometric isomers in pure form or as a mixture, as well as its possible addition salts with a pharmaceutically-acceptable acid or base.

3. A compound as claimed in claim 1 in which R.sub.2 represents cyclopentyl, its possible optical and/or geometric isomers in pure form or as a mixture, as well as its possible addition salts with a pharmaceutically-acceptable acid or base.

4. The compound as claimed in claim 1 which is 7-O-(2-oxopropyl)-3'-O-cyclopentyl-diosmetin.

5. The compound as claimed in claim 1 which is 7-O-ethoxycarbonylmethyl-3'-O-cyclopentyldiosmetin.

6. The compound as claimed in claim 1 which is 7-O-(N,N-dimethylaminocarbonylmethyl)-3'-O-cyclopentyldiosmetin.

7. The compound as claimed in claim 1 which is 7-O-(N-methoxy-N-methylamino-carbonylmethyl)-3'-O-cyclopentyldiosmetin.

8. The compound as claimed in claim 1 which is 7-O-(N-methylaminocarbonylmethyl)-3'-O-cyclopentyldiosmetin.

9. The compound as claimed in claim 1 which is 7-O-(N,N-dimethylaminocarbonylmethyl)-3'-O-(exo-2-norbornyl)diosmetin.

10. A method for treating a living body afflicted with a condition requiring a Group IV phosphodiesterase inhibitor comprising the step of administering to the living body an amount of a compound of claim 1 which is effective for alleviation of said conditions.

11. A pharmaceutical composition useful as a Group IV phosphodiesterase inhibitor method comprising as active principle an effective amount of a compound as claimed in claim 1, together with one or more pharmaceutically-acceptable excipients or vehicles.